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Synthesis and potential spectrum of biological activities of glycoconjugates derivatives of hydroxy-2-methylquinoline carboxylic acids

Katarzyna Malarz 1Marta Musioł 2Robert Musiol 1Gabriela Pastuch-Gawołek 2Maciej Serda 1Ewelina Spaczyńska 1

1. University of Silesia, Institute of Chemistry (UŚ), Szkolna 9, Katowice 40-006, Poland
2. Silesian University of Technology, Department of Organic Chem., Bioorganic Chem. and Biotechnol., Krzywoustego 4, Gliwice 44-100, Poland


Molecules containing quinoline fragment are present in many natural and synthetic drugs covering a broad spectrum of activity of anticancer, antifungal and antiviral effects [1,2]. Unfortunately, compounds designed on the core of quinoline moiety still suffer from poor bioavailability. This encouraged us to introduce the sugar part into the backbone fragment of quinoline to improve the bioavailability of quinoline derivatives. Sugar part could be connected to quinoline derivatives by amide, ester, thioester or glycosidic bond. Based on this assumption, we received a whole range of glycoconjugates quinoline derivatives, which were subjected the biological tests.

Novel series of quinoline based compounds have been tested for antiproliferative activity. The cytotoxicity tests were performed using MTS assay with doxorubicin as the reference. They were found to be active against HCT116 p53+/+and p53 -/- cancer cell lines. Moreover we have tested their activity against human dermal fibroblast to determine their selectivity. This preliminary results have showed us a high potency of synthesized compounds for inhibitions cancer cell lines. Thus further investigations of these compounds should be conducted.

Molecular modelling and 3D QSAR COMFA studies have been performed using TRIPOS SYBYL 2.0 programme running on Intel Pentium based machine under the Debian GNU/Linux operating system. Preliminary results have showed that biological activity of synthesized compounds might be through the competitive inhibition of acetylglucosaminyltransferase enzyme.


R.M. acknowledges the NCN grant 2013/09/B/NZ7/00423.


[1] Musiol, R.; Jampilek, J.; Buchta, V.; Silva, L.; Niedbala, H.; Podeszwa., B.; Palka, A.; Majerz-Maniecka, K.; Oleksyn, B.; Polanski, J., Bioorg. Med. Chem., 2006, 14, 3592-3598.

[2] Majerz-Maniecka, K.; Musiol, R.; Skórska-Stania, A.; Tabak, D.; Mazur, P.; Oleksyn, B.; Polanski, J., Bioorg. Med. Chem., 2011, 19, 1606-1612.


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Submitted: 2014-03-15 13:07
Revised:   2014-05-02 17:11